Hydrochloric Acid → HCID 57565584, compound

HRID 1727027Notes

Reaction equation

N[C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18]3[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])[C:15]3[C:14](=[O:26])[N:13]([CH3:27])[C:12](=[O:28])[N:11]([CH3:29])[C:10]=3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl.N([O-])=[O:32].[Na+]>O>[Cl:25][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([F:24])[C:18]=1[CH2:17][N:16]1[C:15]2[C:14](=[O:26])[N:13]([CH3:27])[C:12](=[O:28])[N:11]([CH3:29])[C:10]=2[N:9]=[C:8]1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:32])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 8-(3-aminophenyl)-7-(2-chloro-6-fluorobenzyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione (88 mg, 0.21 mmol) in 310 μL water was treated with concentrated HCl and then sodium nitrite (19 mg, 0.23 mmol) dissolved in ˜300 μL water. The reaction mixture was stirred at 0° C. for 30 min and then heated to 100° C. for 15 min. The reaction mixture was cooled, dried under reduced pressure, and purified by preparative thin layer chromatography (silica gel, 1 mm plate, EM Science 20×20 cm silica gel 60 F264) eluting with EtOAc:hexane (2:1) to give 37 mg (43% yield) of the title compound as a pale orange solid: 1H NMR (CDCl3, 400 MHz) 7.22-7.16 (m, 1H), 7.12-7.01 (m, 2H), 6.96-6.91 (m, 2H), 6.86-6.81 (m, 1H), 6.80-6.74 (m, 1H), 5.82 (s, 2H), 3.60 (s, 3H), 3.37 (s, 3H); MS (ESP+) m/e 415 (MH+); TLC (EtOAc:hexanes/2:1) Rf=0.41.

Workup

temperatureheated to 100° C. for 15 min
temperatureThe reaction mixture was cooled
customdried under reduced pressure
custompurified by preparative thin layer chromatography (silica gel, 1 mm plate, EM Science 20×20 cm silica gel 60 F264)
washeluting with EtOAc:hexane (2:1)

Sources & evidence

ORD record: ord-4457fd29fb97481ea3bc7c35d89611ef
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495004B2

Reaction notes

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